Process for making turpentine substitute and product therefrom



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WILLIAM BURNS LOGAN, OF QUINCY, LOUISIANA, ASSIGNOR TO ACME PRODUCTS COMLANY, INC., 013 NEW ORLEANS, LOUISIANA, A CORPORATION OF LOUISIANA.

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To all whom it may concern:

Be it known that I, WILLIAM BURNS LOGAN, a citizen of the United States, residing atDe Quincy, in the parish of Calcasieu and State of Louisiana, have invented certain new and useful Improvements in Processes for Making Turpentine Substitute and Product Therefrom, of whichthe following is a specification. .The present invention relates to a novel turpentine substitute and to a process of that pine oil can be convertsuitable for use as a turby a simple and eficient process as described below, the urpentin e substitute being for practically al of the uses of turpentine, as good as actual gum turpentine, and can be produced at a some-.

what lower cost.

In carrying out theprocess of the present invention, l vaporize the pine oil, either 'fractionally or instantaneously in a suitable boiler or still. The vapors of the pine oil are'then conducted through a contact chamher in which they are subjected to the action of a catalyzer, the catalyzer-consistin preferably of a chloride of copper, an especially cuprous chloride, although cupric chloride canalso be used as well as aluminum chloride, and many other metal chlorides. Hydrochloric acid can also be employed. The temperature at'which the pine oil vapor is subjected to the action of the catalyzer should not be below 225 C., nor above 350 6., and in order to produce the 455 best results I prefer to maintain the tern-- perature of the catalyzer chamber at about 250 to 275 C. At the temperatures stated, the-major part of the terpineol and some of the borneol are dehydrated and produce dipentene and other terpenes. the most favorable temperature range, some of the fen'chylalcohol seems to be converted into dipentene. At temperatures below 225 C. the reaction does not seem to take place Also within to any substantial extent, and at temperav Application filed November 23, 1922. I Serial No. 802,887.

tures above 350 (1, other undesirable reactions take place to a considerable extent, wh1ch produce products having objectionable odors. Even at temperatures between 275 and 350 (3., there are some products formed having objectionable odors.

The vapors leaviiig the catalyzer chamber are then conducted to a condenser in which all of the vapors are condensed or asmuch as possible of the vapors are condensed, thereby producing a liquid, which hpon standing settles into two layers, an aqueous layer, and an oily layer. The aqueous layer is removed and discarded. The oily layer, which consists ofa mixture of unconverted pine oil and turpentine substitute, is then subjected to fractional distillation, and the portion which passes over below 200 (3., is separately collected, and this constitutes the turpentine substitute. The residue from the distillation can be rerun through the catalyzer chamber or can be used for any other suitable purpose.

As is-well known, pine oil is a liquid having a specific gravity between about .93 and 9% generally averaging about .933. The turpentine substitute prepared from ordinary pine oil, when subjected to fractional distillation, will produce about of the terpenes of the pine oil, in the form of turpentine substitute. This turpentine substitute containsabout dipentene. It will begin to' boil at about (3., and about 75% of it will distill over below 0., and about95% of it will distill over below 0. Its specific gravity will be found to be between .85 and .86. Its index of refraction will be about 1.475 to 1.477 at 20 C. The liquid will be of the same color as standard gum turpentine or standard wood turpentine. I

The odor of this new turpentine substitute is similar to that of wood turpentine,,.with usually a noticeableodor of limonene. However when temperaturesgabout 275 C. are

used in the catalyzer chamber, small quanr 'tities of other terpene 'compounds are produced which have an unpleasant odor.

The catalyzer as has been stated contains in all cases a chloride, either a metal chloride or hydrochloric acid. Cuprous chloride has given the most favorable results, and this can be used alone as the catalyzer or canibe precipitated upon, suitable carriers, such as ground pumice or silico-gel, or time mesh are copper gauze, The use of a carrier material for the active catalyzer is advisable, as giving more extended surface contact. The pine oil apparently must be in the form of a vapor and so far as I have been able to ascertain the reaction will not take place with the pine oil in a liquid form. If the vapors of pine oil are diluted, by mixing any vapors or other inert liquids, such as water or other oils, or inert gaseasuch as nitrogen, vthe re action will still take place but much more slowly, Hydrochloric acid is less suitable as a c-atalyzer, since even at the preferred temperatures, it-produces a small quantity of bad smelling terpene compounds.

It will be understood that the invention is not restricted to thespecific details above given, but the invention embraces modifications within the scope of the appended claims. I b

The chemical composition of gum and wood turpentine is principally pinene'; gum turpentine containing about 95 per icent pinene, wood turpentine 85 per cent, the re- 7 maining being other terpenes.

The special turpentlne made from pine voil-the principal constituent will be dipen 'tene', amounting to about '90 per cent of its volume, the remainder being a mixture of other'terpenes. Its specific between .85 and .80. Its index and refraction will be about1475 to 1.477 at 20 defractionally distilling the condensate, and,

collecting the fraction distilling up to about 200 C. Y

gravity will fall whereby dipe'ntene resales 2., A process of malringa turpentine sub stitute which comprises subjecting vapors of pine oil.to the action of a catalyst comprisfrom, fractionally distilling the condensate,

and collecting the fraction distilling up to about 200 C.

3. A process of making a turpentine substitute which comprises subjecting vapors of pine oil to the action of a catalyst comprisingia copper chlorid, at a temperature be tween'about 250 and about 275 C.

4. A process which comprises subjecting vapors of pine oil to the action of a catalyst. comprising a chlorid at about 225 to 350 C.

5. A process which comprises subjecting vapors of pine oil to the action of a catalyst I comprising a chlorid, at about 250 to 275 C. l

' 6. A process which comprises subjecting vapors ofpine il tofthe action of alc-atalyst comprsing a copper chlorid, atab'out 225 to 3500 V v.414: v

vapors of pine oil to the action of a catalyst comprising 'cuprous chloridat about 225 to 350C. I 7 I 8. A turpentine substitute, which comi spa, 7. A process which comprisessubjecting prises a liquid material of'turpentine like appearance, having a specific gravity/f between .85 and'.86, containing about of dipentenes, having an index of refraction of about 1.475 to 1.477 at 20 C. ,such material boiling at about (3., about "75% of the whole boiling below ing at not above C.

9. 'A process which comprises passing 'vapors containing terpineol 1n" contactwith a chlorid catalyst between 225 and 350 (1., whereby dipentene compounds are formed.

10. A process which comprises passing Q, and 95 boil-Q vapors containing terpineol in contact wit a chloridcatalyst between'250 and 275 G, 90

compounds are formed.

BURNS LOGAN; 

